This invention relates to pyrazolidinones and, more particularly, to 3-pyrazolidinone carboxyamides which are prostaglandin antagonists.
U.S. Pat. No. 3,873,566 discloses and claims compounds of the general formula ##STR1## where A can be CH.dbd.CH, C.tbd.C or C.sub.6 H.sub.4 ;
R can be H, alkali metal, amine salt and alkyl and cycloalkyl each with up to 12 carbons; PA1 m is 0 or 1; PA1 n and p are 0 to 6; PA1 Y and Z are 0 or H.sub.2, with the proviso that where one is O, the other is H.sub.2 ; PA1 R.sup.1 is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sup.2 is H, CH.sub.3, C.sub.2 H.sub.5, CH.dbd.CH.sub.2 or C.tbd.CH; PA1 R.sup.3 is H or alkanoyl of 2 to 4 carbons; PA1 R.sup.4 and R.sup.5 are H, F, CH.sub.3 or C.sub.2 H.sub.5 and PA1 Q is H, CH.sub.3, CF.sub.2 CH.sub.3 or CF.sub.3. PA1 A is CH.dbd.CH, C.tbd.C, or phenylene; PA1 m is 0-1; PA1 n is 1-5, with the proviso that when m.dbd.0, n is 5 and when m=1 and A is CH.dbd.CH or C.tbd.C, n is 3, and when A is phenylene, n is 1, 2 or 3; PA1 Y and Z are either the same or different and are selected from H, C.sub.1 -C.sub.12 straight-chained or branched-chain alkyl; PA1 R.sup.1 is H, CH.sub.3, C.sub.2 H.sub.5, CH.dbd.CH.sub.2, or C.tbd.CH; PA1 R.sup.2 is H, F, or CH.sub.3 ; PA1 R.sup.3 is H, F, or CH.sub.3, with the proviso that when R.sup.1 .noteq. H, R.sup.2 and R.sup.3 are H; PA1 s is 3-6; and PA1 T is H, CF.sub.2 CH.sub.3, or CF.sub.3 ;
It is stated that some of the esters and acids disclosed therein inhibit or prevent experimentally-induced ulcers in rats. It is also taught that some of the esters are prostaglandin antagonists in in vitro tests employing strips of rat uterus.
U.S. Pat. No. 4,032,533 discloses 3,4-disubstituted-1,3,4-thiadiazoline-2,5-diones of the formula ##STR2## and states that the compounds are prostaglandin mimics or prostaglandin inhibitors.
German Pat. No. 2,735,904 relates to compounds of the formula ##STR3## where, among other things, A and B are single or double bonds, U is ##STR4## R.sup.2 is phenyl or phenoxy, and Q is ##STR5## R.sub.4 being selected from COR.sub.5 and SO.sub.2 R.sub.5 where R.sub.5 is phenyl or alkyl of 1-5 carbons. These compounds are imides and are described as having prostaglandin activities which are more selective, powerful and longer lasting than the natural compounds and as having anti-ulcer and vasodilating effects.
None of these patents indicates that the compounds of this invention would exhibit prostaglandin antagonist activity.